MIL So I had a weird thing proposed to me the other day.

Out to dinner with my aunt and uncle in Oakland (rich bitches, bought me a ticket to the Elite Eight games, and offered to take me to Indy for the Final Four if i could get leave - which i can't).

Uncle asked me if i was planning on making a career out of the military, which seemed to be completely out of left field.

Aunt went on to tell me that they've been talking about who will take over their telecommunications company when they retire. Uncle said that I've got the tech knowledge, and he can teach me everything I need to know businesswise.

They said I'd start out low in the company (20 person company or so), so I could learn the entire company in and out. They'd keep promoting me as time went on, until they were ready to retire (both in their late 50's/early 60's). My Aunt then said she'd make sure I was living comfortably the whole time (they drive an X5 and a mercedes, and keep a new BMW in the garage at work "in case of an emergency". Also live in a $2 million house in Los Angeles.)

Reenlisting is starting to become a fuzzy proposition. I love the military, but I'd also love living back home (los angeles)

at the same time, serving is the best thing I've ever done for myself :/

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Yeah I understand, serving is great.. It's different from other things you do, but just note it down as a great fucking memory for life. Then go make some serious bank with the company, and make another great fucking memory for life.

would, but the closest reserve base is about 2 1/2 hours from where i'd live (Los Angeles)

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meh people drive further distances to my guard unit. Its only one weekend a month. I would honestly do it. Its a once in a lifetime opportunity. Air Force has been good to you broly, but now its time to move on

You need to evaluate what you consider "successful".
If your view of success conjures images of a huge home, (or homes, or estate/estates), brand new cars, designer clothes, etc, then you should consider taking the career opportunity offered by your aunt and uncle, because, as you know, you won't be able to achieve those things in a mil career.
Weigh the good points and the bad. (How will you be viewed by co-workers at the new job? Will they assume you've always had things handed to you? Will you care?)
When you imagine telling your grandchildren about the things you did in your life, what do you picture telling them?
Since much of your career has involved a lot of travel, how are you going to handle being in the same place every single day?
What are your options if it turns out that you can't handle, (or hate), this job- for whatever reason?

Based on first hand experience and observations, the truely self made work far more than they play, or spend time with their family.
If one is born into money, there are often trade offs or strings attached to family offers. Accepting a job, or the good old trust fund, sometimes gives a certain amount of control away, (even after the benefactor passes away), so you need to explore those types of issues, as well.